Cis–trans Isomerisation of CpRe(CO)2(H)(ArF) (ArF = C6FnH5−n; n = 0–5) is the rate determining step in C–H activation of fluoroarenes: A DFT study

Journal of the Chemical Society. Dalton Transactions

Volumn 3, Issue 21, 2003, Pages 4065-4074

  Clot, Eric ^a   Oelckers, Beatriz ^b   Klahn, A Hugo ^b   Eisenstein, Odile ^a   Perutz, Robin N ^c  

^a UNIV MONTPELLIER   (France)

^b PONTIFICIA UNIVERSIDAD CATÓLICA DE VALPARAÍSO   (Chile)

^c UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Dalton discussion no. 6; Density functional calculations; Kinetics; Mechanisms in solution; Organometallic

Indexed keywords

ACTIVATION ENERGY; BENZENE; BINDING ENERGY; COORDINATION REACTIONS; DISSOCIATION; FREE ENERGY; ISOMERIZATION; MIXTURES; OXIDATION; PHASE TRANSITIONS; REACTION KINETICS; THERMODYNAMIC PROPERTIES;

DENSITY FUNCTIONAL THEORY; ENERGY BARRIERS; FLUOROARENES; OXIDATIVE ADDITION;

RHENIUM COMPOUNDS;

EID: 0242443186     PISSN: 14779226     EISSN: None     Source Type: Journal    
DOI: 10.1039/b305064e     Document Type: Article

References (66)

1. G.W. Parshall: Acc. Chem. Res. (1975), 8: 113.
2. R.H. Crabtree: Chem. Rev. (1985), 85: 245.
3. B.A. Arndtsen, R.G. Bergman, T.A. Mobley, T.H. Peterson: Acc. Chem. Res. (1995), 28: 154.
4. A.E. Shilov, G.B. Shul’pin: Chem. Rev. (1997), 97: 2879.
5. J.A. Labinger, J.E. Bercaw: Nature (2002), 417: 507.
6. W.D. Jones: Top. Organomet. Chem. (1999), 3: 9.
7. D.D. Wick, W.D. Jones: Organometallics (1999), 18: 495.
8. J.L. Bennett, P.T. Wolczanski: J. Am. Chem. Soc. (1997), 119: 10696.
9. G.W. Parshall: Acc. Chem. Res. (1970), 3: 139.
10. W.D. Jones, F.J. Feher: Acc. Chem. Res. (1989), 22: 91.
11. M. Lavin, E.M. Holt, R.H. Crabtree: Organometallics (1989), 8: 99.
12. L. Dong, S.T. Belt, S.B. Duckett, M.G. Partridge, W.D. Jones, R.N. Perutz: J. Chem. Soc., Chem. Commun. (1991), 266.
13. R.M. Chin, L. Dong, S.B. Duckett, M.G. Partridge, W.D. Jones, R.N. Perutz: J. Am. Chem. Soc. (1993), 115: 7685.
14. A. Vigalok, O. Uzan, L.J.W. Shimon, Y. Ben-David, J.M.L. Martin, D. Milstein: J. Am. Chem. Soc. (1998), 120: 12539.
15. A.J. Toner, S. Gründemann, E. Clot, H.-H. Limbach, B. Donnadieu, S. Sabo-Etienne, B. Chaudret: J. Am. Chem. Soc. (2000), 122: 6777.
16. D.G. Gusev, M. Maddot, F.M. Dolgushin, K.A. Lyssenko, M.Y. Antipin: Organometallics (2000), 19: 1734.
17. L. Johansson, M. Tilset, J.A. Labinger, J.E. Bercaw: J. Am. Chem. Soc. (2000), 122: 10846.
18. T.H. Peterson, J.T. Golden, R.G. Bergman: J. Am. Chem. Soc. (2001), 123: 455.
19. S. Reinartz, P.S. White, M. Brookhart, J.L. Templeton: J. Am. Chem. Soc. (2001), 123: 12724.
20. C.M. Norris, S. Reinartz, P.S. White, J.L. Templeton: Organometallics (2002), 22: 5649.
21. W.D. Jones: Acc. Chem. Res. (2003), 36: 140.
22. R.M. Bullock, C.E.L. Headford, K.M. Henessy, S.E. Kegley, J.R. Norton: J. Am. Chem. Soc. (1989), 111: 3897.
23. C. Hall, R.N. Perutz: Chem. Rev. (1996), 96: 3125.
24. S.E. Bromberg, H. Yang, M.C. Asplund, T. Lian, B.K. McNamara, K.T. Kotz, J.S. Yeston, M. Wilkens, H. Frei, R.G. Bergman, C.B. Harris: Science (1997), 278: 260.
25. A. Chernega, J. Cook, M.L.H. Green, L. Labella, S.J. Simpson, J. Souter, A.H.H. Stephens: J. Chem. Soc., Dalton Trans. (1997), 3225.
26. C.L. Gross, G.S. Girolami: J. Am. Chem. Soc. (1998), 120: 6605.
27. S. Geftakis, G.E. Ball: J. Am. Chem. Soc. (1998), 120: 9955.
28. B.K. McNamara, J.S. Yeston, R.G. Bergman, C.B. Moore: J. Am. Chem. Soc. (1999), 121: 6437.
29. D.C. Grills, X.Z. Sun, G.I. Childs, M.W. George: J. Phys. Chem. A (2000), 104: 4300.
30. T.O. Northcutt, D.D. Wick, A.J. Vetter, W.D. Jones: J. Am. Chem. Soc. (2001), 123: 7257.
31. H. Gérard, O. Eisenstein, D.-H. Lee, J. Chen, R.H. Crabtree: New J. Chem. (2001), 25: 1121.
32. H.C. Lo, A. Haskel, M. Kapont, E. Keinan: J. Am. Chem. Soc. (2002), 124: 3226.
33. M.C. Asplund, P.T. Snee, J.S. Yeston, M.J. Wilkens, C.K. Payne, H. Yang, K.T. Kotz, H. Frei, R.G. Bergman, C.B. Harris: J. Am. Chem. Soc. (2002), 124: 10605.
34. D.G. Churchill, K.E. Janak, J.S. Wittenberg, G. Parkin: J. Am. Chem. Soc. (2003), 125: 1403.
35. C.L. Higgitt, A.H. Klahn, M.H. Moore, B. Oelckers, M.G. Partridge, R.N. Perutz: J. Chem. Soc., Dalton Trans. (1997), 1269.
36. F. Godoy, C.L. Higgitt, A.H. Klahn, B. Oelckers, S. Parsons, R.N. Perutz: J. Chem. Soc., Dalton Trans. (1999), 2039.
37. J.J. Carbó, O. Eisenstein, C.L. Higgitt, A.H. Klahn, F. Maseras, B. Oelckers, R.N. Perutz: J. Chem. Soc., Dalton Trans. (2001), 1452.
38. H. van der Heijden, A.G. Orpen, P. Pasman: J. Chem. Soc., Chem Commun. (1985), 1576.
39. A.A. Bengali, A. Leicht: Organometallics (2001), 20: 1345.
40. E. Clot, M. Besora, F. Maseras, C. Mégret, O. Eisenstein, B. Oelckers, R.N. Perutz: Chem. Commun. (2003), 490.
41. A.D. Selmeczy, W.D. Jones, M.G. Partridge, R.N. Perutz: Organometallics (1994), 13: 522.
42. W.D. Harman: Chem. Rev. (1997), 97: 1953.
43. H.V.R. Dias, Z. Wang, W. Jin: Inorg. Chem. (1997), 36: 6205.
44. A.A. Bengali: Organometallics (2000), 19: 4000.
45. S.H. Meiere, B.C. Brooks, T.B. Gunnoe, E.H. Carrig, M. Sabat, W.D. Harman: Organometallics (2001), 20: 3661.
46. C.N. Iverson, R.J. Lachicotte, C. Muller, W.D. Jones: Organometallics (2002), 21: 5320.
47. A.A. Bengali, T.F. Stumbaugh: Dalton Trans. (2003), 354.
48. R.G. Ball, A.K. Campen, W.A.G. Graham, P.A. Hamley, S.G. Kazarian, M.A. Ollino, M. Poliakoff, A.J. Rest, L. Sturgeoff, I. Whitwell: Inorg. Chim.Acta (1997), 259: 137.
49. F. Weinhold, in Encyclopedia of computational chemistry, ed. P. von R. Schleyer, John Wiley & Sons, Chichester, 3rd edn., (1998), 1792.
50. B.E.R. Schilling, R. Hoffmann, D.L. Lichtenberger: J. Am. Chem. Soc. (1979), 101: 585.
51. B.E.R. Schilling, R. Hoffmann, D.L. Lichtenberger: J. Am. Chem. Soc. (1979), 101: 585.
52. H. Lesnard, I. Demachy, Y. Jean, A. Lledós: Chem. Commun. (2003), 850.
53. J.W. Faller, A.S. Anderson: J. Am. Chem. Soc. (1970), 92: 5852.
54. R. Poilblanc, P. Kalck, R. Prince, J. Roussel: J. Organomet. Chem. (1970), 24: 445.
55. T.C. Flood, E. Rosenberg, A. Sarhangi: J. Am. Chem. Soc. (1977), 99: 4334.
56. P. Kubacek, R. Hoffmann, Z. Havlas: Organometallics. (1982), 1: 180.
57. C.P. Casey, R.S. Tanke, P.N. Hazin, C.R. Kemnitz, R.J. McMahon: Inorg. Chem. (1992), 31: 5474.
58. R.S. Bogadi, D.C. Levendis, N.J. Coville: J. Am. Chem. Soc. (2002), 124: 1104.
59. N.J. Coville, D.C. Levendis: Eur. J. Inorg. Chem. (2002), 3067.
60. R.N. Perutz and B. Oelckers, unpublished results.
61. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr. R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle and J.A. Pople, GAUSSIAN 98 (Revision A.7), Gaussian, Inc., Pittsburgh, PA, (1998).
62. A.D.J. Becke: J. Chem. Phys. (1993), 98: 5648.
63. J.P. Perdew, Y. Wang: Phys. Rev. B (1992), 82: 284.
64. D. Andrae, U. Häussermann, M. Dolg, H. Stoll, H. Preuss: Theor. Chim. Acta (1990), 77: 123.
65. A.W. Ehlers, M. Böhme, S. Dapprich, A. Gobbi, A. Höllwarth, V. Jonas, K.F. Köhler, R. Stegmann, A. Veldkamp, G. Frenking: Chem. Phys. Lett. (1993), 208: 111.
66. P.C. Hariharan, J.A. Pople: Theor. Chim. Acta (1973), 28: 213.